Sodium ethanethiolate → HCID 59124153, compound

Participants

Reaction Steps

A solution of (2S)-(+)-3-[2,2-dimethyl-4-(4-methoxybenzo[b]thiophen-2-yl)piperidin-1-yl]-1-(2-methylbenzofuran-4-yl)oxy-2-propanol (0.750 g, 1.56 mmol) and sodium ethanethiolate (2.10 g, 25.0 mmol) in DMF (26 mL) was heated at 90° C. for 14 h and concentrated under reduced pressure. The residue was then diluted with 50 mL of brine and extracted with CH2Cl2 (3×50 mL). The organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography [0 to 6% (2.0 M NH3 in MeOH)/CH2Cl2]. The residual DMF was removed as an azeotrope with xylenes and re-run through a column of silica gel [3.5% (2.0 M NH3 in MeOH)/CH2Cl2] to give the title compound as an off-white foam (0.2751 g, 37%). IR (KBr) 3593, 2969, 2936, 1281, 1085 cm−1. Ion Spray MS 466.2 (M+H)+; 464.3 (M−H)−. [α]D=55.26 (c 0.5791, MeOH). C27H31NO4S.0.2CH2Cl2

Provenance & Evidence